CA2046532C - Process for warp-free pigmenting of polyolefins - Google Patents
Process for warp-free pigmenting of polyolefins Download PDFInfo
- Publication number
- CA2046532C CA2046532C CA002046532A CA2046532A CA2046532C CA 2046532 C CA2046532 C CA 2046532C CA 002046532 A CA002046532 A CA 002046532A CA 2046532 A CA2046532 A CA 2046532A CA 2046532 C CA2046532 C CA 2046532C
- Authority
- CA
- Canada
- Prior art keywords
- pigment
- process according
- coated
- polyolefins
- warp
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 21
- 230000000485 pigmenting effect Effects 0.000 title claims abstract description 7
- 229920006112 polar polymer Polymers 0.000 claims abstract description 14
- 239000012860 organic pigment Substances 0.000 claims abstract description 11
- 239000002245 particle Substances 0.000 claims abstract description 9
- 239000000049 pigment Substances 0.000 claims description 80
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 30
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 29
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 23
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 8
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 8
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 229920001903 high density polyethylene Polymers 0.000 claims description 3
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims description 3
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004700 high-density polyethylene Substances 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- YKPJEYXZEBLYCI-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole Chemical compound C1=NC=C2C=NC=C21 YKPJEYXZEBLYCI-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000725 suspension Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- GMZBMXSSGCHKEM-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)pyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C1=CC(Cl)=CC=C1C1=NC(=O)C2=C1C(=O)N=C2C1=CC=C(Cl)C=C1 GMZBMXSSGCHKEM-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920000058 polyacrylate Polymers 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 polyethylene Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 2
- IWVKTOUOPHGZRX-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(=O)C(C)=C IWVKTOUOPHGZRX-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000004349 Polyvinylpyrrolidone-vinyl acetate copolymer Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- ARVNHJBMBBFPCP-UHFFFAOYSA-L [OH-].[OH-].[Ra+2] Chemical compound [OH-].[OH-].[Ra+2] ARVNHJBMBBFPCP-UHFFFAOYSA-L 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000549 coloured material Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- VPWFPZBFBFHIIL-UHFFFAOYSA-L disodium 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidonaphthalene-2-carboxylate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000019448 polyvinylpyrrolidone-vinyl acetate copolymer Nutrition 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/08—Ingredients agglomerated by treatment with a binding agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2998—Coated including synthetic resin or polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH231390 | 1990-07-11 | ||
| CH2313/90-5 | 1990-07-11 | ||
| CH299090 | 1990-09-14 | ||
| CH2990/90-3 | 1990-09-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2046532A1 CA2046532A1 (en) | 1992-01-12 |
| CA2046532C true CA2046532C (en) | 2002-05-21 |
Family
ID=25690099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002046532A Expired - Fee Related CA2046532C (en) | 1990-07-11 | 1991-07-09 | Process for warp-free pigmenting of polyolefins |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US5274010A (cs) |
| EP (1) | EP0466646B1 (cs) |
| JP (1) | JP3157193B2 (cs) |
| KR (1) | KR100187309B1 (cs) |
| BR (1) | BR9102916A (cs) |
| CA (1) | CA2046532C (cs) |
| CZ (1) | CZ282436B6 (cs) |
| DE (1) | DE59108114D1 (cs) |
| ES (1) | ES2091314T3 (cs) |
| MX (1) | MX9100130A (cs) |
| SK (1) | SK281000B6 (cs) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9117765D0 (en) * | 1991-08-16 | 1991-10-02 | Ciba Geigy Ag | Method of improving storage stability |
| US6005025A (en) | 1992-11-17 | 1999-12-21 | General Electric Company | Method of dispersing solid additives in polymers and products made therewith |
| US5679148A (en) * | 1993-01-12 | 1997-10-21 | Ciba-Geigy Corporation | Pigment compositions of a diketopyrrolopyrrole and an aminoalkyl acrylate resin |
| DE59400199D1 (de) * | 1993-02-09 | 1996-05-23 | Ciba Geigy Ag | Mit Silanen beschichtete organische Pigmente |
| DE4313090A1 (de) * | 1993-04-22 | 1994-10-27 | Basf Ag | Verfahren zum verzugsfreien Pigmentieren von hochpolymeren organischen Materialien |
| JPH0781239A (ja) * | 1993-09-17 | 1995-03-28 | Nippon G Ii Plast Kk | レーザーマーキング用樹脂組成物 |
| EP0656402B1 (de) * | 1993-12-01 | 2000-12-20 | Ciba SC Holding AG | Pigmentzusammensetzung aus modifiziertem Diketopyrrolopyrrol und Aminoalkylacrylatharz |
| DE59409405D1 (de) * | 1993-12-01 | 2000-07-27 | Ciba Sc Holding Ag | Pigmentzusammensetzung aus Diketopyrrolopyrrol und Aminoalkylacrylatharz |
| DE59409309D1 (de) * | 1993-12-22 | 2000-05-31 | Ciba Sc Holding Ag | Mit Zirkonium oder Titan-Phosphatkomplexen beschichtete organische Pigmente |
| JPH08205733A (ja) * | 1995-02-02 | 1996-08-13 | Kureha Gosen Kk | 釣糸用着色組成物および当該組成物によって被覆された釣糸 |
| US6103782A (en) * | 1996-07-29 | 2000-08-15 | Marconi Data Systems, Inc. | Method of making dry pigment surface modified with polyethylene coating |
| IN220164B (cs) * | 1997-09-08 | 2008-07-11 | Ciba Geigy Ag | |
| US6063182A (en) * | 1997-09-08 | 2000-05-16 | Ciba Speciality Chemicals Corporation | Stir-in pigment compositions |
| EP1041095B1 (en) * | 1997-12-19 | 2006-02-22 | Matsumoto Yushi-Seiyaku Co., Ltd. | Synthetic organic particles and process for the production of the same |
| US6379456B1 (en) * | 1999-01-12 | 2002-04-30 | Halliburton Energy Services, Inc. | Flow properties of dry cementitious and non-cementitious materials |
| US6245142B1 (en) | 1999-01-12 | 2001-06-12 | Halliburton Energy Services, Inc. | Flow properties of dry cementitious materials |
| US6660080B2 (en) | 1999-01-12 | 2003-12-09 | Halliburton Energy Services, Inc. | Particulate flow enhancing additives |
| KR100359469B1 (ko) * | 2000-02-18 | 2002-11-07 | 주식회사 폴리코 | 폴리올레핀 부직포의 날염처리방법 |
| KR20000049510A (ko) * | 2000-03-29 | 2000-08-05 | 류종원 | 바실러스 나토와 약초를 이용한 기능성 된장, 청국장조성물 및 제조방법 |
| US6503970B1 (en) | 2000-09-29 | 2003-01-07 | Engelhard Corporation | Co-processed pigments |
| US20040266918A1 (en) * | 2001-10-24 | 2004-12-30 | Paolo Balliello | Method for producing a granular formulation of plastic-soluble colorants |
| DE10204275A1 (de) | 2002-02-02 | 2003-08-07 | Clariant Gmbh | Verfahren zum verzugsfreien Pigmentieren von teilkristallinen Kunststoffen mit Phthalocyaninpigmenten |
| BR0311950A (pt) * | 2002-06-19 | 2005-03-29 | Ciba Sc Holding Ag | Composições de pigmento que não produzem empenamento contendo pigmentos ftalocianinas |
| DE10235573A1 (de) | 2002-08-03 | 2004-02-12 | Clariant Gmbh | Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolpigmenten zum verzugsfreien Pigmentieren von teilkristallinen Kunststoffen |
| CN100400603C (zh) * | 2002-12-04 | 2008-07-09 | 西巴特殊化学品控股有限公司 | 通过喷雾干燥可得到的无尘色料组合物 |
| CA2516268A1 (en) * | 2003-02-20 | 2004-09-02 | Ciba Specialty Chemicals Holding Inc. | Easily dispersible pigment composition |
| DE10338730A1 (de) | 2003-08-21 | 2005-03-24 | Clariant Gmbh | Verfahren zum verzugsfreien Pigmentieren von teilkristallinen Kunststoffen mit Phthalocyaninpigmenten |
| EP1939258B1 (en) * | 2003-12-19 | 2014-01-22 | Novartis AG | Method for preparing preconditioned pigment particles |
| WO2006111493A2 (en) * | 2005-04-21 | 2006-10-26 | Ciba Specialty Chemicals Holding Inc. | Pigment formulations |
| US7476443B2 (en) * | 2005-09-19 | 2009-01-13 | Kimberly-Clark Worldwide, Inc. | Photo-stable and surface-functionalizable colorant particles |
| PL1790696T3 (pl) * | 2005-11-28 | 2013-09-30 | Agfa Nv | Niewodne dyspersje pigmentowe zawierające specyficzne synergetyki dyspersji |
| DE102006034239A1 (de) * | 2006-07-25 | 2008-01-31 | Clariant International Limited | Farbige wässrige Polymerdispersion, deren Herstellung und Verwendung |
| JP2010507698A (ja) * | 2006-10-25 | 2010-03-11 | チバ ホールディング インコーポレーテッド | 熱安定性のカプセル化顔料 |
| US8154289B2 (en) * | 2008-04-11 | 2012-04-10 | The General Hospital Corporation | Method for joint sparsity-enforced k-space trajectory and radiofrequency pulse design |
| US20090137172A1 (en) * | 2008-12-04 | 2009-05-28 | Lei Huang | Colorant media and articles having photo-stable and surface-functionalizable colorant particles |
| US20110184096A1 (en) * | 2010-01-25 | 2011-07-28 | Sivapackia Ganapathiappan | Coated pigment composition |
| US8309630B2 (en) * | 2010-01-25 | 2012-11-13 | Hewlett-Packard Development Company, L.P. | Polymer-encapsulated pigment |
| US20150118494A1 (en) | 2012-05-09 | 2015-04-30 | Sun Chemical Corporation | Surface modified pigment particles, method of preparation & application thereof |
| US9913781B2 (en) * | 2013-06-13 | 2018-03-13 | Kao Corporation | Detergent composition comprising polyvinyl alcohol-containing pigment granules |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3085989A (en) * | 1958-02-20 | 1963-04-16 | Cabot Corp | Process for incorporating a polymercoated acidic pigment in polyethylene |
| US3956230A (en) * | 1968-02-01 | 1976-05-11 | Champion International Corporation | Compatibilization of hydroxyl-containing fillers and thermoplastic polymers |
| BE793704A (fr) * | 1972-01-05 | 1973-07-05 | Hoechst Ag | Procede de preparation de compositions renfermant de l'alcool polyvinylique et un pigment |
| US3806464A (en) * | 1972-04-05 | 1974-04-23 | Du Pont | Pigment encapsulated with an acrylic interpolymer |
| US3904562A (en) * | 1973-01-31 | 1975-09-09 | Sherwin Williams Co | Organic pigments encapsulated with vinylpyrrolidone polymer |
| US4049615A (en) * | 1973-07-30 | 1977-09-20 | Ciba-Geigy Corporation | Process for the distortion-free coloration of polyolefins with organic pigments |
| US4107133A (en) * | 1974-01-14 | 1978-08-15 | Dainippon Ink & Chemicals, Inc. | Colored polyethylene molding compositions |
| JPS5650741B2 (cs) * | 1974-11-20 | 1981-12-01 | ||
| GB2052520A (en) * | 1979-06-25 | 1981-01-28 | Trimetal Paint Co Belgium Nv | Coating compositions and coatings comprising polymer-transition metal chelates |
| DE3121765A1 (de) * | 1981-06-02 | 1982-12-16 | Basf Ag, 6700 Ludwigshafen | Waessrige pigmentpasten und deren verwendung |
| DE3143609A1 (de) | 1981-11-03 | 1983-05-11 | Kraftwerk Union AG, 4330 Mülheim | Analysenmanipulator zur zerstoerungsfreien werkstoffpruefung und verfahren zur koordinatensteuerung desselben |
| US4771086A (en) * | 1982-09-02 | 1988-09-13 | Union Carbide Corporation | Encapsulating finely divided solid particles in stable suspensions |
| DE3327562A1 (de) * | 1983-07-30 | 1985-02-07 | Basf Ag, 6700 Ludwigshafen | Zubereitungen von leicht verteilbaren isoindolinpigmenten und deren verwendung |
| DE3613257A1 (de) * | 1986-04-19 | 1987-10-22 | Basf Lacke & Farben | Neue pigmentpraeparationen, enthaltend ein organisches pigment, ein verfahren zu ihrer herstellung und ihre verwendung zur einfaerbung von thermoplastischen kunststoffen |
| US4983661A (en) * | 1987-05-28 | 1991-01-08 | Ferro Corporation | Non plateout molding composition |
| US4808230A (en) * | 1987-06-16 | 1989-02-28 | Ciba-Geigy Corporation | Organic pigments coated with metal oxides fixed with ethyl cellulose |
| US4889562A (en) * | 1987-06-16 | 1989-12-26 | Ciba-Geigy Corporation | Organic pigments coated with crosslinked ethyl cellulose |
| US4957949A (en) * | 1987-10-29 | 1990-09-18 | Matsui Shikiso Chemical Co., Ltd. | Thermochromic color masterbatch |
| JPH0692546B2 (ja) * | 1988-06-16 | 1994-11-16 | 昭和アルミパウダー株式会社 | 着色メタリック顔料およびその製造方法 |
-
1991
- 1991-07-02 EP EP91810518A patent/EP0466646B1/de not_active Expired - Lifetime
- 1991-07-02 ES ES91810518T patent/ES2091314T3/es not_active Expired - Lifetime
- 1991-07-02 DE DE59108114T patent/DE59108114D1/de not_active Expired - Lifetime
- 1991-07-02 KR KR1019910011170A patent/KR100187309B1/ko not_active Expired - Lifetime
- 1991-07-05 US US07/726,055 patent/US5274010A/en not_active Expired - Lifetime
- 1991-07-09 CA CA002046532A patent/CA2046532C/en not_active Expired - Fee Related
- 1991-07-09 MX MX9100130A patent/MX9100130A/es not_active IP Right Cessation
- 1991-07-10 BR BR919102916A patent/BR9102916A/pt not_active IP Right Cessation
- 1991-07-10 CZ CS912135A patent/CZ282436B6/cs not_active IP Right Cessation
- 1991-07-10 SK SK2135-91A patent/SK281000B6/sk unknown
- 1991-07-11 JP JP17026791A patent/JP3157193B2/ja not_active Expired - Lifetime
-
1993
- 1993-10-15 US US08/138,537 patent/US5401780A/en not_active Expired - Lifetime
-
1994
- 1994-12-20 US US08/359,710 patent/US6180694B1/en not_active Expired - Lifetime
-
2000
- 2000-10-13 US US09/687,898 patent/US6288142B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR920002675A (ko) | 1992-02-28 |
| ES2091314T3 (es) | 1996-11-01 |
| CZ282436B6 (cs) | 1997-07-16 |
| JPH04226542A (ja) | 1992-08-17 |
| JP3157193B2 (ja) | 2001-04-16 |
| DE59108114D1 (de) | 1996-10-02 |
| US5401780A (en) | 1995-03-28 |
| US5274010A (en) | 1993-12-28 |
| US6180694B1 (en) | 2001-01-30 |
| SK281000B6 (sk) | 2000-10-09 |
| CA2046532A1 (en) | 1992-01-12 |
| KR100187309B1 (ko) | 1999-05-15 |
| MX9100130A (es) | 1992-02-28 |
| US6288142B1 (en) | 2001-09-11 |
| CS213591A3 (en) | 1992-02-19 |
| EP0466646B1 (de) | 1996-08-28 |
| EP0466646A1 (de) | 1992-01-15 |
| BR9102916A (pt) | 1992-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |